It's not so much that the Chicago Cubs have not won a World Series since 1908 that frustrates me. It's not that they failed to make the World Series once since 1945 (when most of the good players were in the military). It's that they looked so bad doing it.
The Cubs rebounded from early- to mid-season disasters, rallied into first place and survived a sweep by the Florida Marlins in the final week of the regular season (while Milwaukee folded) to win their division. They earned a playoff berth for the first time since their 2003, when they faded just a handful of outs from the World Series.
They worked that hard just for the right to look that bad in the playoffs?
Granted, the Cubs barely won more than they lost in the regular season. They were in a weak division. They were not favored going into the post-season. But that didn't stop the St. Louis Cardinals in 2006, when they stumbled into the playoffs but then won the whole thing. Lots of wild card teams have won the whole thing.
Some teams have rebuilding years. For the Cubs, it's a rebuilding century. Since their 1908 win, the Cubs are 0-7 in World Series appearances (1910, 1918, 1929, 1932, 1935, 1938 and 1945).
Now, going into the 2008 season, Cub fans can look forward to countless references to the fact that this will be the 100th season since their last World Series victory. I can't wait.